Arsenical compound.



86 of the substances described in our aforesaid UNITED STATES ATENT wAnTEn A. JAooBs, or MOUNT vEE oN, AND WADE 1;. BROWN, MICHAEL IEID E nEneEn, AND LOUISE PEAEQE, on NEW YORK, ZN.Y., AssIoNonsTo; TI'IER'QGKE- EELLEN. INSTITUTE FOR MEDICAL nEsEAnon, on NE worm, N.-Y.,"'A' contou TIoN on NEW YORK. w l

ABSENIGAL COMPOUND.

1,280,122. Specification of Letters Patent. Patented S t; 24 p r- Application filed 0mm 3, 1917. Serial No. 194,462. To all whom it may concern: reacting the amino henylarsinoxids with Be it known that we, WAIJIER A. JACOBS the corresponding aalogcnacylaniinocom- Ph. D., resldin at Mount Vernon, Westpound, such as, for example,,chloroacetyl ohester county, ew York, WADE H. BROWN, anilin, etc. i t 5 M. D., residing at Flushing in'the city of The following examples will make clear New York, borou h of Queens, Queens the method of reparation and general char- (lzplllmt NewdYorli, tfioH EL linkmnanYnsnllz, acter of the su stances discovered.

res1 mg n e c1t 0 ew or borough of Manhattan, couiity and State of Ewmnple I (P w '1 'f 10 New York, and LOUISE PEARCE, M. D., residphenylgzymmmding in the city of New York, borou h of A =0 Manhattan, count and State of New ork, all citizens of the nited States, have jointly invented a new and Improved Arsenical 16 Compound, of which the following is a specification.

In our co-pendin applications, Serial Nos. H NH, 19%,459 and 194,4 1, we have described a class of arsenical compounds of use in the 20" tre tment of trypanosomal orspirochaetal infactions, composed of an aromatic arsonic acid possessing an a-aminoacylamin side chain, the. 'aromatic nucleus containing the 7 grams of N- (phenyl-p-arson'ic acid) -aarsenic being joined. 0 he iro g P phenylglycinamid of the following formula 26 in said side chain. We have found that by sub'ecting the organic arsonic acids descri ed in our said. (so-pending applications AME to the action of mild reducing agents, the arsonic acid residue can be smoothly con- 50 verted into the arsinoxid radical without altering the remainder of the molecule. As a resu t, in the new type of substances so obtained the chemical groupings which char acterized the organic portion of the molecule co-pending applications were retained, but at the same time in maifi; instances the therapeutic efliciency of e parent sub.- taneeswas tly improved. are suspended in cc. hydrochloric acid 40 su stances were also obtained by (1.12 sp. gm), treated with} cc. of 48 er 50 cent. h driodio acid and a concentrated solumixture.

After half an hour the lrvdrochlorid of the oxid is filtered off and washed with hydrochloric acid (1.12 sp. gr.). The product is sus ended in water and ice and ammonium hy roxid is added until the mixture is permanently alkaline to litmus. The oxid, which forms a white flocculent precipitate, is filtered ofi and thoroughly washed with ice water. For urification it is dissolved. in cold dilute sodium h droxid solution and reprecipitated by the a dition of ammonium chlorid solution. The dry powder is almost insoluble .in cold water, melting under hot water. It dissolves readily in methyl and ethyl alcohols and acetone.

ECHI- CO tween 120 and 155C. t is smoothly oxidized in alkaline solution by hydrogen peroxid to the arsonic acid.

Ewample III-IV-(PhenyZ-p-afsinowiM glycyl-m'-amiaophenol.

Aa=0 I i 9 Q I i 7.5 grams N- (phenyl-p-arsonic acid)- glycyl-m-aminophenol are suspended in 150 cc. hydrochloric acid (sp. 'gr. 1.12), a concentrated solution of 1 gram sodium iodld added, and then in small portions, with vlgorous stirring, a concentrated sodium bisulfite' solution'is added until the reaction is completed. The completion is indicated by the permanent disappearance of free iodin and by the presence of SO, in excess. The thick microcrystalline mass is filtered oil and washed with hydrochloric acid (sp. gr. 1.12), and the mass, after suspension in-ice water, is carefully neutralized with ammonia. The white flocculent precipitate of oxid is fil tered and repurified as in the above examples.

This oxid, when dry, forms a white powder, sparingly soluble in water, but it dissolves easily in dilute alkalis, alcohol, methyl alcohol, acetone and glacial acetic acid. It slowly sinters above 130 0., and is completely melted only above 200.

Ewample I V-N (Phenyl-p-ao-sirwwid) -ghl0- yZa/ntkranibic Q QOOE HOB SO H precipitate is then suspended in ice water and dissolved byadding sodium hydroxid in sllght excess. The oxid is obtained by cautious addition of dilute acetic acid as long as a white flocculent precipitate is formed. This is filtered and thoroughly washed with water. When freshly precipitated it dissolves easily in cold alcohol, but when dry warming is necessary. It is read- 11y soluble in dilute alkalis and carbonates.

The foregoing are a few examples of substances falling within the spirit and scope of our invention. It will be obvious to anyone skilled in the. art that many variations in the exact constitution of the substances described may be made without departing from the spirit and scope of our invention.

I What we claim is:

1. As a new product, an aromatic arsin- Y oxid having in its molecule an a-aminoacylaniin side chain, the aromatic nucleus oon- 10 3.'As a new produqt, an N- (aryl a rsin- WALTEKLJAOOBSJE. D.

momma v I 3 taining the aqseniq being joined to the 5. As a new product,,N-(phenyl-p-arsina-ammo group 1n smd slde chum. oxid) -glycyl'-m'-aminophenol 2. As a. new roduct, an aromatic arsin- =0 oxid having in lts molecule an a-aminoacyll'arylumin side chain having the eneral formula, NHCHR ONHAr, in w ich'R may be alkylor aryl or hydrogen and Ar is dq; slubstituted or unsubstituted aromatic m we oiid)I-glycyloxyary1amm. 1 WADE H. BROWN, I. D. v

v 4'. As a new product, an N- ('phenyl arsinv HIOIIAEL HEIDBLBEIGEB, Pu. D.

oXid)-'glycylaminophenol.' w LOUISE PEARCE. I. D.

Copies ettml petal: my be obtained terlve ante ml, by droning the MM 0! rebate,

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